Halogen pyrimidinyl aryl (thio)ethers as pesticides

Abstract

The invention relates to novel halogenopyrimidines, to two processes for their preparation and to their use as pesticides.

What is claimed is:  
     
       1. A compound of the formula (I)                    
       wherein 
       Z represents a moiety selected from the group consisting of cycloalkyl having 3 to 7 carbon atoms which is in each case unsubstituted or mono- to disubstituted by halogen, alkyl or hydroxyl; thienyl, pyridyl or furyl, which in each case is unsubstituted or substituted by alkyl having 1 to 4 carbon atoms; and phenyl or naphthyl, each of which is unsubstituted or mono- to tetrasubstituted by identical or different substituents, the substituents selected from the group consisting of:  
       halogen, cyano, nitro, amino, hydroxyl, formyl, carboxyl, carbamoyl, thiocarbamoyl; straight-chain and branched alkyl, hydroxyalkyl, oxoalkyl, alkoxy, alkoxyalkyl, alkylthioalkyl, dialkoxyalkyl, alkylthio, alkylsulphinyl and alkylsulphonyl having in each case 1 to 8 carbon atoms;  
       straight-chain and branched alkenyl and alkenyloxy having in each case 2 to 6 carbon atoms; straight-chain and branched halogenoalkyl, halogenoalkoxy, halogenoalkylthio, halogenoalkylsulphinyl and halogenoalkylsulphonyl having in each case 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms;  
       straight-chain and branched halogenoalkenyl and halogenoalkenyloxy having in each case 2 to 6 carbon atoms and 1 to 11 identical or different halogen atoms;  
       straight-chain and branched alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, arylalkylaminocarbonyl, dialkylaminocarbonyloxy, alkenylcarbonyl and alkynylcarbonyl having 1 to 6 carbon atoms in the hydrocarbon chains; cycloalkyl and cycloalkyloxy having in each case 3 to 6 carbon atoms;  
       alkylene having 3 or 4 carbon atoms, oxyalkylene having 2 or 3 carbon atoms and dioxyalkylene having 1 or 2 carbon atoms, each of which is attached doubly and in each case which is unsubstituted or mono- to tetrasubstituted by identical or different substituents from the group consisting of fluorine, chlorine, oxo, methyl, trifluoromethyl and ethyl; and a grouping                    
        wherein  
       A 1  represents hydrogen, hydroxyl or alkyl having 1 to 4 carbon atoms and  
       A 2  represents hydroxyl, amino, methylamino, benzyl; unsubstituted or cyano-, hydroxyl-, alkoxy-, alkylthio-, alkylamino-, dialkylamino- or phenyl-substituted alkyl or alkoxy having 1 to 4 carbon atoms; alkenyloxy or alkynyloxy having in each case 2 to 4 carbon atoms; phenyl, phenoxy, phenylthio, benzoyl, benzoylethenyl, cinnamoyl, phenylalkyl, phenylalkyloxy, phenylalkylthio, 5,6-dihydro-1,4,2-dioxazin-3-ylmethyl, triazolylmethyl, benzoxazol-2-ylmethyl, 1,3-dioxan-2-yl, benzimidazol-2-yl, dioxol-2-yl and oxadiazolyl, having in each case 1 to 3 carbon atoms in the alkyl moiety and each of which is unsubstituted or mono- to trisubstituted in the ring moiety by a substituent selected from the group consisting of halogen and straight-chain and branched alkyl and alkoxy having 1 to 4 carbon atoms,  
       R represents hydrogen or methyl,  
       Q represents oxygen or sulphur and  
       X represents fluorine, chlorine, bromine or iodine,  
       L 1 , L 2 , L 3  and L 4  are identical or different and, independently of one another, each represents hydrogen, halogen, cyano, nitro, or represent alkyl, alkoxy, alkylthio, alkylsulphinyl or alkylsulphonyl having in each case 1 to 6 carbon atoms and being in each case unsubstituted or substituted by 1 to 5 halogen atoms.  
     
     
       2. The compound of claim  1  wherein 
       Z represents a moiety selected from the group consisting of cyclopentyl or cyclohexyl, each of which is unsubstituted or mono- to disubstituted by fluorine, chlorine, methyl, ethyl or hydroxyl; unsubstituted or methyl- or ethyl-substituted thienyl, pyridyl or furyl; phenyl or naphthyl, each of which is unsubstituted or mono- to tetrasubstituted by identical or different substituents, the substituent selected from the group consisting of  
       fluorine, chlorine, bromine, iodine, cyano, nitro, amino, hydroxyl, formyl, carboxyl, carbamoyl, thiocarbamoyl; methyl, ethyl, n- and i-propyl, n-, i-, s- and t-butyl, 1-, 2-, 3-, neo-pentyl, 1-, 2-, 3-, 4-(2-methylbutyl), 1-, 2-, 3-hexyl, 1-, 2-, 3-, 4-, 5-(2-methylpentyl), 1-, 2-, 3-(3-methylpentyl), 2-ethylbutyl, 1-, 3-, 4-(2,2-dimethylbutyl), 1-, 2-(2,3-dimethylbutyl); hydroxymethyl, hydroxyethyl; 3-oxobutyl, methoxymethyl, dimethoxymethyl, methoxy, ethoxy, n- and i-propoxy; methylthio, ethylthio, n- and i-propylthio; methylsulphinyl, ethylsulphinyl, methylsulphonyl and ethylsulphonyl; vinyl, allyl, 2-methylallyl, propen-1-yl, crotonyl, propargyl; vinyloxy, allyloxy, 2-methylallyloxy, propen-1-yloxy, crotonyloxy, propargyloxy; trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, trifluoromethylthio, difluorochloromethylthio, trifluoromethylsulphinyl or trifluoromethylsulphonyl; methylamino, ethylamino, n- and i-propylamino, dimethylamino, diethylamino; acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, methylaminocarbonyl, ethylaminocarbonyl, dimethylaminocarbonyl, diethylaminocarbonyl, dimethylaminocarbonyloxy, diethylaminocarbonyloxy, benzylaminocarbonyl, acryloyl, propioloyl, cyclopentyl, cyclohexyl; propanediyl, ethyleneoxy, each of which is doubly attached and in each case unsubstituted or mono- to tetrasubstituted by identical or different substituents from the group consisting of fluorine, chlorine, oxo, methyl and trifluoromethyl; and a grouping                    
        wherein  
       A 1  represents hydrogen, methyl or hydroxyl and  
       A 2  represents hydroxyl, methoxy, ethoxy, amino, methylamino, benzyl or hydroxyethyl; or phenyl, phenoxy, phenylthio, benzoyl, benzoylethenyl, cinnamoyl, benzyl, phenylethyl, phenylpropyl, benzyloxy, benzylthio, 5,6-dihydro-1,4,2-dioxazin-3-ylmethyl, triazolylmethyl, benzoxazol-2-ylmethyl, 1,3-dioxan-2-yl, benzimidazol-2-yl, dioxol-2-yl, oxadiazolyl, each of which is unsubstituted or mono- to trisubstituted in the ring moiety by a substituent selected from the group consisting of halogen and straight-chain or branched alkyl or alkoxy having 1 to 4 carbon atoms,  
       R represents hydrogen or methyl,  
       Q represents oxygen or sulphur and  
       X represents fluorine or chlorine and  
       L 1 , L 2 , L 3  and L 4  are identical or different and, independently of one another, each represents hydrogen, fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl or ethylsulphonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy difluoromethylthio, difluorochloromethylthio, trifluoromethylthio, trifluoromethylsulphinyl or trifluoromethylsulphonyl.  
     
     
       3. A compound of the formula (I) according to claim  1  wherein Q represents oxygen. 
     
     
       4. A compound of the formula                    
     
     
       5. A microbiocidal composition comprising a microbicidally effective amount of a compound according to claim  1  and an inert diluent. 
     
     
       6. A method of combating undesired microorganisms comprising the step of applying a microbicidally active amount of a compound according to claim  1  to such microorganisms and/or to their habitat.